I suppose if you're fully closeted you don't have to worry about this one. If you're like me, only out to close people but go out from time to time, the opportunity might present itself with strangers. (Especially if they ask: Why do you do it? You know, reply with: Have you ever tried it? So how do you know you won't like it?) If you're out to the world, of course, there's nothing really holding you back.
For me I would probably not do it for fear of getting someone else caught in this web. You know, they try it, like it and get stuck in it as well. I used to believe you are either a crossdresser or not, which meant you started on this path somewhere before twenty. With what I've read on so-called "late bloomers" I'm not so sure any more. Some will argue it lay dormant and was triggered by something, which implies the trigger was there all along. Others will argue it popped out of nowhere. (Sounds a bit like that other nonsensical theory: Nothing exploded and created everything). Either way I'd prefer not to be the one sending someone down this path, the price it extols on the person, his family, his marriage and/or relationships is too high, and I would not want to be the person responsible, even if it's a stranger.
What's your take?